Importance. Professional orientation in pedagogical fields is an effective means for the education system development. The diagnosis is an essential planning and organization component of targeted professional orientation for high school pupils. The issue of conscious selection of a teaching career is linked to the axiological aspect of the orientation for adolescents and young people, as well as to the implementation of the individualization and differentiation principles in education. A comprehensive set of diagnostic tools for targeted career guidance for high school students under modern conditions, considering the pedagogical field and its axiological significance, has not yet been defined. There is a growing need for educational initiatives and scientific support for the development of methods range for targeted career guidance, including diagnostics, to encourage students to pursue careers in the field of education. The aim of the research is to provide a theoretical basis and present the results of developing diagnostic tools for organizing differentiated professional orientation for high school students pursuing pedagogical studies. Based on systematic, predictive, individualized, and value-based approaches to professional guidance, these diagnostic tools could be useful for selecting students for teaching positions, implementing a system of personalized career counseling in a contemporary educational setting, and for admission officers involved in planning and executing career guidance programs in the field of teacher training.Research Methods. Analysis of scientific literature and the current state of affairs in the vocational guidance and career counseling field, as well as a review of existing tools and parameters for this purpose. The research follows a logical path that begins with the career guidance organization for schoolchildren and progresses to the diagnostic instruments development (such as sample interview questions) for use in differentiated career counseling for those interested in teachingrelated fields.Results and Discussion. The “professional orientation” concept is considered both in Russia and abroad, and the specific implementation examples of career guidance activities in education are presented. An important area of professional orientation is value orientation towards pedagogical specialties. Career guidance diagnostics includes an analysis of values, value attitude to the profession, interests, abilities, and orientation of students necessary to predict the development of personality qualities in the chosen field of training in pedagogical specialties, and the organization of differentiated career guidance. In the research course, the author’s diagnostic tools are developed – the diagnostic matrix “Career guidance interview for a future teacher”.Conclusion. The problem of differentiated professional orientation towards pedagogical specialties among adolescents and young people is urgent and requires special attention from the state, society and the educational system. The professional orientation of high school students to pedagogical specialties includes the diagnosis of values, value attitude to the chosen profession, individual interests and abilities, improves educational results and helps to see the prospects and opportunities of everyone in the future professional field – the field of education. In addition, it reduces the risk for a person to choose an unsuitable profession and helps to successfully integrate into the professional teaching community in the future.